Unchecked items do not play in iTunes

Q: My wife and I share an iTunes library. I have an iPod classic which syncs everything in the library and my wife uses an iPod nano (video) and syncs only the checked songs. When I use my Apple Remote with iTunes on my iMac and I push the “next button” it skips to the next CHECKED song rather than the actual next song. Is there any way to change this?

– Patrick

A: This is actually by design, and is one of the oft-misunderstood aspects of syncing only checked songs. Generally, UNchecking songs should only be used for music that you don’t want to listen to via iTunes. This can be a great feature for seasonal music, for instance (ie, to keep all of the Christmas music out of your playlists for the 10 months of the year that you don’t want to hear it). As you have observed, however, if you’re going to listen to your music through iTunes itself, it creates a problem. Tracks that are UNchecked will not be played as part of any playlist, Party Shuffle, or any other playback sequence. They will only be played if they are selected specifically.

There is no way around this feature itself, as this is the way iTunes is designed to work. However, the good news is that you can change the way in which you synchronize your wife’s iPod nano. Instead of synchronizing only checked items, try creating a set of playlists for the music that should be transferred to her iPod, and then set her iPod to synchronize only those specific playlists. You can then leave ALL of your music in your iTunes library checked without having to worry about it not playing back.

The easiest way to do this is to create a playlist, or a set of playlists, and list all of the music that you want kept on your wife’s iPod in these playlists. Note you can also store these in a single playlist folder for easy reference.

Once these playlists are set up, then simply connect your wife’s iPod and select the “Music” tab from the iPod settings:

Choose “Selected Playlists” and then simply choose the specific playlists that you have set up and click the “Apply” button. Only the tracks that are in those playlists will be synchronized with the iPod, and any tracks NOT in those playlists will be removed from the iPod.

Once this is working the way you want, you can REcheck all of the previously-unchecked content in your iTunes library and it will still not be transferred to her iPod nano unless it is also listed in one of the synced playlists. Note that you can quickly check/uncheck all displayed tracks at once by holding down the CMD (Mac) or CTRL (Windows) key while clicking on a checkbox beside a track.

Further, here’s another hint you might find useful in setting up these initial playlists: Since you’re already using checked tracks, you can build a quick Smart Playlist that gives you a list of all of your checked tracks as a starting point. To do this, simply choose File, New Smart Playlist from the iTunes menu, and set the criteria similar to the following:

This will produce a playlist that includes only your checked tracks. While this won’t work in the long-run (since eventually you’re going to check ALL of your tracks), you could easily copy this information to a standard playlist as a starting point by selecting all of the tracks displayed in that playlist and then choosing File, New Playlist from Selection. You could then choose to sync ONLY that new standard playlist to the iPod nano, and you’d have a very quick and easy starting point without having to manually sift through dozens of tracks and add them to playlists manually.

Note that Smart Playlists offer another useful advantage to synchronizing using selected playlists rather than checked items. The check boxes in iTunes themselves are static, whereby a Smart Playlist could be used to create a dynamic music rotation that updates itself every time your wife syncs her iPod, using information such as the number of times a track has been played, when it was last listened to, when it was added to the library, what the rating of the track is, and more.